How to Transcend the Fundamentals?

Knowing when to ignore your experience is the true sign of experience. -JOHN MAEDA

On October 26, 1914, Ernest Shackleton, captain of the Endurance, set sail with a crew of twenty-seven men comprising the Imperial Trans-Antarctic Expedition. Their goal was to complete the first land crossing of the Antarctic. With an expedition of this difficulty, there was no shortage of planning or coordinating involved.

Shackleton’s final itinerary planned to take the Endurance into the Weddell Sea before disembarking near Vahsel Bay with a team of six men and seventy dogs to sledge across the Antarctic. At the same time, a second ship directly across the continent would sail into the Ross Sea, setting down provisions along the intended route for Shackleton and crew. This would keep the men supplied until they reached their final destination at the McMurdo Sound base.

Ten days after setting sail from Buenos Aires, the Endurance reached South Georgia and received disheartening news at the whaling station. The conditions in the Weddell Sea were the worst in recent memory. As the Endurance continued south towards the Weddell Sea, they learned this first hand.

In an open ocean the Endurance covered close to 200 miles a day. But facing polar pack ice they were slowed to a crawl and by December covered less than thirty miles a day.

As they came within 200 miles of Vahsel Bay, fierce winds struck and they were forced to shelter the Endurance next to a large iceberg. After six days, on January 24, 1915, the winds began to subside but the Endurance was frozen solid in pack ice as far as the eye could see.

The crew did their best to free the ship, chipping away at ice with chisels and saws. But after a month, the ship was still trapped. As the days grew shorter, Shackleton knew there was no immediate way out and no way to communicate with the outside world.

Shackleton’s neatly made plans to cross the Antarctic came to an abrupt halt. It was now about survival and the preservation of his crew, which demanded an entirely new set of strategies. He gave the order to prepare for winter aboard the Endurance.

On the open sea, each man had their assignment. There was work to be done and they remained in good spirits. But with the ship out of commission, there wasn’t as much work to be done. Shackleton feared demoralization more than the threat of ice or sub-zero temperatures.

In an effort to keep the crew engaged and morale high, Shackleton directed the construction of “dogloos” on the ice to protect the dogs. He sent others hunting to secure a supply of meat for the winter. And he created a series of social occasions with grog on Saturday nights, music on Sunday nights, and dog-sledding races. The men remained in surprisingly strong spirits throughout the depths of winter.

But when spring arrived, the Endurance showed no signs of breaking loose. Quite the opposite. After being trapped in pack ice for nine months, the Endurance was being slowly crushed by the Weddell Sea. On October 27, 1915, Shackleton gave the order to abandon ship.

While sheltered aboard the Endurance, they had room to store equipment for every imaginable scenario. But Shackleton recognized they were in a new territory of survival which would require sacrificing preparedness for speed. There was no room left for luxuries.

Shackleton urged the crew to leave behind anything that wasn’t absolutely essential for survival. To emphasize the seriousness of his request, he tore a page from the Book of Job, placed his Bible in the snow, and set off without looking back.

Shackleton and the crew huddled to set up camp on a large nearby ice floe. They hoped the drift would carry them towards the safety of Paulet Island, 250 miles away. Despite the dire circumstances, the men were relieved to have a plan. The indecision and speculation aboard the Endurance was over. Shackleton knew not to let ambiguity linger for too long.

Even as storms carried the floe in unexpected directions, Shackleton operated with conviction. Whether in demanding patience during the drift or taking deliberate action to relocate camp and board the lifeboats during a last-ditch effort to reach land.

As conditions changed, Shackleton’s strategies would shift. But he remained purposeful in his every move. The crew held a deep respect and admiration for this. It’s what held them together during their bleakest moments.

It took everything he had, but nearly two years after setting sail aboard the Endurance, Shackleton reached the shore of South Georgia Island with five of his men in the last remaining lifeboat. The rest of the crew remained on Elephant Island where they were rescued three months later.

What does this story teach us?

There are times to ignore advice – favouring nuance in one situation, simplicity in another. Once you understand this, you can begin looking for inflection points.

When Shackleton gave the order to winter aboard the ship, he shifted his strategy from one of operations and efficiency, to survival and engagement. With polar nights and a perpetual darkness bearing down on them, he knew the real enemy was a sense of restlessness and complacency among the crew.

Nine months later when they abandoned the ship, Shackleton had to pivot again, favoring speed over preparedness. It was the opposite of his strategy while originally planning the expedition or aboard the ship, but he knew time was of the essence. Every spare second wasted hauling around non-essential equipment could mean the difference between life and death.

Strategies are frameworks to help improve your judgment, decision making, and ability to think further ahead. But they won’t provide a checklist of prescribed actions for your every move in life. As Shackleton knew well, no matter how strategic you are, there’s no replacement for true resourcefulness. And this is where people get lost. The map is not the territory.

It’s easy to get locked into a rigid thought process with a single strategy if you stick to the map without ever looking up. But when you stop reaching for absolutes, you’re able to embrace the motion inherent to life. Everything is fluid.

There’s no one-size-fits-all solution hiding out there. Specific advice should be approached with caution. The likelihood that the exact sequence of actions and events that worked for someone else will line up the same way for you isn’t close to zero – it is zero.

You must create space for your own interpretation. Without this, it’s impossible to know when to ignore advice or swallow your pride and take a different approach.

Nothing about life is neat or orderly. It’s full of contradictions, exceptions, and ambiguity. But if you’re able to establish a stronger sense of independence and practice decisiveness in pivotal moments, you can build quiet confidence within the grey area where most of life takes place.

If you have any hopes of contributing something meaningful of your own, it starts here. Only a true master of strategy is able to identify an exception, break with the fundamentals, and make their own way.